I've used a lot of averages (average playoff window, average window of SC winning teams, and what year of the window teams won the cup) and discovered that most teams win the SC 4.97778 years into their window and are most likely to win the cup from years 5-11 of the playoff window. According to this the Bruins and Leafs are most likely to win the SC, with the Avalanche, Knights and Jets in the second tier of likely hood, and the Hurricanes, Panthers, and Oilers are in the third tier of least likely to win the SC. I've made a google Spreadsheet of all SC winners of the NHL Salary Cap era here: https://docs.google.com/spreadsheets/d/1-TrMCdLQfPzzLqKYh7Bdxw2AIn42nmZO5iVtDq19Lfw/edit?usp=sharing